Laboratoire de Glycochimie, des Antimicrobiens
et des Agroressources UMR 7378 CNRS


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Actualités et Publications

Synthesis and interfacial properties of new 6-sulfate sugar-based anionic surfactants,

Abdellahi, B.; Bois, R.; Golonu, S.; Pourceau, G.; Lesur, D.; Chagnault, V.; Drelich, A.; Pezron, I.; Nesterenko, A.; Wadouachi, A.

Tetrahedron Lett. 2021, 153113.

Three families of anionic sugar-based surfactants bearing a sulfate functional group on the primary position of a monosaccharide were synthesized and their physicochemical properties were compared. The first family corresponds to 6-sulfate derivatives of commercially available octa- and dodecyl β-D-gluco- and galactopyranosides. The second and the third families contain an amide linker between the sulfated monosaccharide (galactose, glucose or xylose) and the hydrophobic alkyl chain. Twelve of the as-synthesized anionic glycolipids, including nine novel sulfated compounds, were investigated for their surface activity at the air/liquid interface and for their self-assembling properties. These sugar-based surfactants show surface properties similar to those of commercial anionic surfactants (SDS and SLES) with good ability to reduce surface tension. The obtained results confirm the interest in these new bio-based molecules for potential substitution of anionic surfactants in various formulations.

One-Pot Synthesis of Asymmetrically Difunctionalized Oligomaltosides by Cyclodextrin Ring Opening,

Pélingre, M.; Smadhi, M.; Bil, A.; Bonnet, V.; Kovensky, J.

ChemistryOpen 2021, 10, 493-496.

Abstract The synthesis of pure difunctionalized hexa-, hepta- and octamaltosides was performed by one-pot chemical reaction from perbenzoylated cyclodextrin. Oligomaltosides with azide, propargyl or allyl on reducing end and an unprotected hydroxyl group on non-reducing end were obtained from perbenzoylated α-, β- and γ-cyclodextrin with 12 to 48 % yields.

Synthesis of new sulfated disaccharides for the modulation of TLR4-dependent inflammation,

Naitaleb, R.; Denys, A.; Allain, F.; Ausseil, J.; toumieux, s.; Kovensky, J.

Org. Biomol. Chem. 2021.

Natural sulfated glycans are key players in inflammation through TLR4 activation, and therefore synthetic exogenous sulfated saccharides can be used to downregulate inflammation processes. We have designed and synthesized new sulfated compounds based on small and biocompatible carbohydrates able to cross the BBB. Suitable protected donor and acceptor, obtained from a unique precursor, have been stereoselectively glycosylated to give an orthogonally protected cellobiose disaccharide. Selective deprotection and sulfation allowed to synthesize four differentially sulfated disaccharides, which have been characterized by NMR, HRMS and MS/MS. Together with their partially protected precursors, the new compounds were tested on HEF-TLR4 cells. Our results show the potential of small oligosaccharides to modulate TLR4 activity, confirming the need of sulfation and the key role of the 6-sulfate groups to trigger TLR4 signalization.

Hybrid Electrolytes Based on Optimized Ionic Liquid Quantity Tethered on ZrO2 Nanoparticles for Solid-State Lithium-Ion Conduction,

Bidal, J.; Becuwe, M.; Hadad, C.; Fleutot, B.; Davoisne, C.; Deschamps, M.; Porcheron, B.; Nhien, A. N. V.

ACS Appl. Mater. Interfaces 2021.

This paper describes the simple, highly reproducible, and robust synthesis of a new solid organic/inorganic electrolyte based on the ionic liquid (IL) 1-butyl-3-(carboxyundecyl)imidazolium bis(trifluoromethylsulfonyl)imide tethered to zirconia nanoparticles (15–25 nm) by coordination and named ZrO2@IL. The IL monolayer formation, ensured by two-dimensional solid-state NMR, at the nanoparticles’ surface considerably reduces both the IL’s consumption and the IL amount at the ZrO2 surface compared to the IL-based hybrid electrolytes reported in the literature. After LiTFSI, used as a lithium source, content optimization (26 wt %), the hybrid exhibits unprecedented stable conductivity passing from 0.6 × 10–4 S.cm–1 to 0.15 × 10–4 S.cm–1, respectively, from 85 °C to room temperature (25 °C). Unlike silica which is commonly adopted for this type of hybrid material, zirconia makes it possible to produce more impact-resistant pellets that are easier to compact, thus being favorable for accurate conductivity studies and battery development by electrode/composite/solid electrolyte layer stacking. The ZrO2@IL/LiTFSI solid hybrid electrolyte’s thermal stability (up to 300 °C) and performance make this electrolyte suitable for lithium conduction in all-solid-state batteries.

CHAPTER 4 Carbon Nanostructures and Polysaccharides for Biomedical Materials,

González-Domínguez, J. M.; Álvarez-Sánchez, M. Á.; Hadad, C.; Benito, A. M.; Maser, W. K.

Carbon Nanostructures for Biomedical Applications 2021, 98-152.

Even though many members from the broad family of carbon nanostructures have been known to us for decades, and despite their promising potential in biology and medicine, there is still a long way ahead to reach the goal of using them in real applications. The cause of such a gap still lies in the persistent drawbacks of insolubility, processability difficulties, poor consistency of macroscopic assemblies and surface inertness of carbon nanostructures. However, solely their direct chemical derivatization might not solve the problem right away. New processing elements need to come into play, but this also twists the whole picture, as the toxicity and performance profiles become more complex. We herein analyse the potential of natural polysaccharides (with a particular focus on cellulose) towards hybrid materials and structures for biomedical purposes. The role that these biopolymers acquire when interfacing with carbon nanostructures goes far beyond a mere dispersing effect, but instead creates unprecedented synergies leading to hydrogels, aerogels, films or fibres with high biocompatibility and bioactivity. In this chapter, the history of carbon nanostructures and natural polysaccharides in the field of biomedical applications will be respectively reviewed, to subsequently go into detail of specific hybrids made with the most relevant biopolymers (namely cellulose, chitin, chitosan and alginate) with extraordinary prospects in biomedicine.

First Steps to Rationalize Host–Guest Interaction between α-, β-, and γ-Cyclodextrin and Divalent First-Row Transition and Post-transition Metals (Subgroups VIIB, VIIIB, and IIB),

Dossmann, H.; Fontaine, L.; Weisgerber, T.; Bonnet, V.; Monflier, E.; Ponchel, A.; Przybylski, C.

Inorg. Chem. 2021, 60, 930-943.

Cyclodextrins (CDs) are cyclic oligosaccharides mainly composed of six, seven, and eight glucose units, so-called α-, β-, and γ-CDs, respectively. They own a very particular molecular structure exhibiting hydrophilic features thanks to primary and secondary rims and delimiting a hydrophobic internal cavity. The latter can encapsulate organic compounds, but the former can form supramolecular complexes by hydrogen-bonding or electrostatic interactions. CDs have been used in catalytic processes to increase mass transfer in aqueous–organic two-phase systems or to prepare catalysts. In the last case, interaction between CDs and metal salts was considered to be a key point in obtaining highly active catalysts. Up to now, no work was reported on the investigation of factors affecting the binding of metal to CD. In the study herein, we present the favorable combination of electrospray ionization coupled to mass spectrometry [ESI-MS(/MS)] and density functional theory molecular modeling [B3LYP/Def2-SV(P)] to delineate some determinants governing the coordination of first-row divalent transition metals (Mn2+, Co2+, Ni2+, Cu2+, and Fe2+) and one post-transition metal (Zn2+) with α-, β-, and γ-CDs. A large set of features concerning the metal itself (ionic radius, electron configuration, and spin state) as well as the complexes formed (the most stable conformer, relative abundance in MS, CE50 value in MS/MS, binding energy, effective coordination number, average bond lengths, binding site localization, bond dissociation energies, and natural bond orbital distribution) were screened. Taking into account all of these properties, various selectivity rankings have been delineated, portraying differential association/dissociation behaviors. Nonetheless, unique 3D topologies for each CD–metal complex were emphasized. The combination of these approaches brings a stone for building a compendium of molecular features to serve as a suitable descriptor or predictor for a better first round rationalization of catalytic activities.

A simple procedure to obtain a medium-size oligogalacturonic acids fraction from orange peel and apple pomace wastes,

Cano, M. E.; García-Martín, A.; Ladero, M.; Lesur, D.; Pilard, S.; Kovensky, J.

Food Chem. 2021, 346, 128909.

Pectin oligosaccharides, which can be obtained from fruit wastes, have proven their potential as plant immune-system elicitors. Although the precise size of active species is still under investigation, medium size oligosaccharides have been reported as the most active. Three defined oligogalacturonic acid (OGAs) mixtures were produced from commercial pectin, orange peel and apple pomace residues. The methodology developed involves two sequential acid treatments followed by stepwise ethanol precipitation. Without the need of chromatographic separations, three different fractions were obtained. The fractions were analyzed by high performance anion exchange chromatography (HPAEC) and were completely characterized by mass spectrometry, showing that the small size, medium size and large size fractions contained OGAs of degree of polymerization 3 to 9, 6 to 18, and 16 to 55, respectively.

Start-up G+Lyte - Trophée de l'innovation dans la catégorie transition énergétique

La start-up G+LYTE, soutenue par le CNRS et CNRS Innovation est lauréate du Trophée de l'innovation dans la catégorie innovation transition énergétique !
Ce prix lui a été décerné par l'agence d'innovation Hauts-de-France Innovation

Graphene quantum dots: From efficient preparation to safe renal excretion,

Hadad, C.; González-Domínguez, J. M.; Armelloni, S.; Mattinzoli, D.; Ikehata, M.; Istif, A.; Ostric, A.; Cellesi, F.; Alfieri, C. M.; Messa, P.; Ballesteros, B.; Da Ros, T.

Nano Research 2020.

Carbon nanomaterials offer excellent prospects as therapeutic agents, and among them, graphene quantum dots (GQDs) have gained considerable interest thanks to their aqueous solubility and intrinsic fluorescence, which enable their possible use in theranostic approaches, if their biocompatibility and favorable pharmacokinetic are confirmed. We prepared ultra-small GQDs using an alternative, reproducible, top-down synthesis starting from graphene oxide with a nearly 100% conversion. The materials were tested to assess their safety, demonstrating good biocompatibility and ability in passing the ultrafiltration barrier using an in vitro model. This leads to renal excretion without affecting the kidneys. Moreover, we studied the GQDs in vivo biodistribution confirming their efficient renal clearance, and we demonstrated that the internalization mechanism into podocytes is caveolae-mediated. Therefore, considering the reported characteristics, it appears possible to vehiculate compounds to kidneys by means of GQDs, overcoming problems related to lysosomal degradation.

Physicochemical, foaming and biological properties of lowly irritant anionic sugar-based surfactants,

Bois, R.; Abdellahi, B.; Mika, B.; Golonu, S.; Vigneron, P.; Chagnault, V.; Drelich, A.; Pourceau, G.; Wadouachi, A.; Vayssade, M.; Pezron, I.; Nesterenko, A.

Colloids and Surfaces A: Physicochemical and Engineering Aspects 2020, 607, 125525.

Surface-active compounds derived from biomass, especially sugar-based amphiphiles, have received wide attention regarding their biodegradability, low toxicity and ecological acceptability. Compared to nonionic sugar-based surfactants, the anionic ones show significantly better solubility, higher surface activity and foaming performance. Thus they are largely used in personal care formulations and many technological applications. However, anionic surfactants are well known to induce skin and eye irritation. In this study, three sugar-based anionic surfactants, bearing a lipidic chain grafted to the anomeric position of a monosaccharide (glucose or xylose) and a sulfate group on the primary hydroxyl, were synthesized: 6-O-sulfo-N-(β-d-glucopyranosyl) dodecanamide (GlcNC12S), N-dodecyl-6-O-sulfo-d-gluconamide (GlcCC12S) and N-dodecyl-6-O-sulfo-d-xylonamide (XylCC12S). These molecules were investigated in details for their self-assembling behavior, foaming properties and biological ef7452fects. All their properties were compared to those of two commercially available anionic surfactants, sodium laureth sulfate (SLES) and sodium dodecylsulfate (SDS). Results revealed that the three anionic glycolipids show surface properties and foaming behavior comparable to those of SDS. Furthermore, their cytotoxic and irritation potentials are significantly lower compared to commercial molecules, which make these renewable molecules potential candidates for replacement of petroleum-based compounds.

Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources
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